I met with a trusted friend and business colleague today (who shall remain nameless until he publishes his book on this topic) because he brought to my attention recently that there is a clear psychology behind every entrepreneur’s reason for which they are just that—their “entrepreneur why”.  He piqued my interest when he mentioned it so I asked if I could take him to lunch to have him uncover mine.

I quickly shared with him that I am acutely aware of my developmental scarring and my rationale behind most choices I make.  I said this because I knew he was about to start asking pointed questions about my childhood, schooling, socialization, early work years, and current work environment. It felt odd to go from the type of lunch meeting I typically have where it’s a two-way dialogue to one that was entirely focused on me being vulnerable about myself and past experiences.

I won’t share here all of the details of what he uncovered, in part because I don’t want to steal his genius that will ultimately become a book, as well as that I don’t feel it necessary to share all of that here.  That being said, there were a couple items that he shared that stood out to me.

The first of note was that he identified that a motivator behind each of my businesses is giving back. He pointed out that I came from a supported background and that whether it’s my payments company that I continue to grow out of motivation to help business owners save money, my networking organization in which I’m driven to make valuable connections for others, or my financial literacy books for kids that aims to help kids have a stronger financial future.  Candidly, this caught me completely by surprise. I recognized from my narrative to him that I said those things, but I was caught off-guard because I’ve never characterized myself as someone who is motivated by helping others. I actually tend to admire people whom I’d define in that way, and out of no place of humility whatsoever, I simply never self-identified in that way.  It was eye-opening to hear someone hear the synopsis of my life story and evaluate that this is my motivation.

He also pointed out to me that I operate my primary business out of a place of security and rule-following.  He challenged me to identify when/where I’d be able to reallocate some/all of my time and energy into the other ones that tap into my “why” more purely.

It’s tough to open up like this to anyone. It’s also tough to hear feedback about yourself that one part surprises you, one part resonates with what you know to be true,  and in last part touches on doubts, questions and/or concerns with which you’ve already been wrestling.  I’m planning to spend some time further thinking through the “why” and other points he shared with me. Some times you just need a little kick-in-the-pants from an outsider to help you see the spot on which you’re standing.